TWI341832B - - Google Patents

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Publication number: TWI341832B
Authority: TW; Taiwan
Prior art keywords: adamantane; formula; represented; crystallization; mass
Prior art date: 2002-07-29

Application number

TW092120550A

Other languages

English (en)

Chinese (zh)

Other versions

TW200403205A (en

Inventor

Jun Mase

Shinji Miyamoto

Akio Kojima

Masao Saito

Original Assignee

Idemitsu Kosan Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2002-07-29

Filing date

2003-07-28

Publication date

2011-05-11

2002-07-29 Priority claimed from JP2002219176A external-priority patent/JP4170696B2/ja

2002-07-30 Priority claimed from JP2002220612A external-priority patent/JP4170697B2/ja

2002-07-30 Priority claimed from JP2002220613A external-priority patent/JP4170698B2/ja

2002-07-30 Priority claimed from JP2002220614A external-priority patent/JP4170699B2/ja

2003-07-28 Application filed by Idemitsu Kosan Co filed Critical Idemitsu Kosan Co

2004-03-01 Publication of TW200403205A publication Critical patent/TW200403205A/zh

2011-05-11 Application granted granted Critical

2011-05-11 Publication of TWI341832B publication Critical patent/TWI341832B/zh

Links

ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 claims description 344
238000002425 crystallisation Methods 0.000 claims description 79
230000008025 crystallization Effects 0.000 claims description 77
239000002904 solvent Substances 0.000 claims description 61
239000007788 liquid Substances 0.000 claims description 59
238000005406 washing Methods 0.000 claims description 56
239000013078 crystal Substances 0.000 claims description 49
238000001035 drying Methods 0.000 claims description 49
238000004519 manufacturing process Methods 0.000 claims description 47
238000006243 chemical reaction Methods 0.000 claims description 38
238000006317 isomerization reaction Methods 0.000 claims description 32
239000003054 catalyst Substances 0.000 claims description 27
238000000034 method Methods 0.000 claims description 24
239000002994 raw material Substances 0.000 claims description 24
238000000926 separation method Methods 0.000 claims description 24
229910052751 metal Inorganic materials 0.000 claims description 22
239000002184 metal Substances 0.000 claims description 22
238000009835 boiling Methods 0.000 claims description 17
239000010457 zeolite Substances 0.000 claims description 17
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
229910021536 Zeolite Inorganic materials 0.000 claims description 16
150000001875 compounds Chemical class 0.000 claims description 16
HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 16
239000001257 hydrogen Substances 0.000 claims description 16
229910052739 hydrogen Inorganic materials 0.000 claims description 16
239000002002 slurry Substances 0.000 claims description 14
238000004821 distillation Methods 0.000 claims description 11
238000005984 hydrogenation reaction Methods 0.000 claims description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 9
238000001816 cooling Methods 0.000 claims description 9
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 8
229910000041 hydrogen chloride Inorganic materials 0.000 claims description 8
238000001953 recrystallisation Methods 0.000 claims description 8
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 7
239000007795 chemical reaction product Substances 0.000 claims description 7
239000010432 diamond Substances 0.000 claims description 7
238000001704 evaporation Methods 0.000 claims description 7
230000008020 evaporation Effects 0.000 claims description 7
-1 trimethylphenylene Chemical group 0.000 claims description 7
150000001335 aliphatic alkanes Chemical class 0.000 claims description 6
MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 6
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 5
150000001342 alkaline earth metals Chemical class 0.000 claims description 5
230000000737 periodic effect Effects 0.000 claims description 5
YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 5
229910052761 rare earth metal Inorganic materials 0.000 claims description 5
150000002910 rare earth metals Chemical class 0.000 claims description 5
HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 claims description 4
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 4
150000001298 alcohols Chemical class 0.000 claims description 4
150000001735 carboxylic acids Chemical class 0.000 claims description 4
239000012452 mother liquor Substances 0.000 claims description 4
229910052707 ruthenium Inorganic materials 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
230000005855 radiation Effects 0.000 claims description 3
239000011029 spinel Substances 0.000 claims description 3
229910052596 spinel Inorganic materials 0.000 claims description 3
LPSXSORODABQKT-UHFFFAOYSA-N tetrahydrodicyclopentadiene Chemical compound C1C2CCC1C1C2CCC1 LPSXSORODABQKT-UHFFFAOYSA-N 0.000 claims description 3
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
230000001376 precipitating effect Effects 0.000 claims 3
238000013019 agitation Methods 0.000 claims 2
150000002431 hydrogen Chemical class 0.000 claims 2
OLWAZOBRCQWWDB-UHFFFAOYSA-N 2,3,4,4a,4b,5,6,7,8,8a,9,9a-dodecahydro-1h-fluorene Chemical compound C12CCCCC2CC2C1CCCC2 OLWAZOBRCQWWDB-UHFFFAOYSA-N 0.000 claims 1
TXTISNNAUQWGPT-UHFFFAOYSA-N 2,3,4-trimethylbenzonitrile Chemical compound CC1=CC=C(C#N)C(C)=C1C TXTISNNAUQWGPT-UHFFFAOYSA-N 0.000 claims 1
ILNYDHOAOJZFFP-UHFFFAOYSA-N anthracene naphthalene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C12.C1=CC=CC2=CC3=CC=CC=C3C=C12.C1=CC=CC2=CC=CC=C12 ILNYDHOAOJZFFP-UHFFFAOYSA-N 0.000 claims 1
HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 claims 1
150000002923 oximes Chemical class 0.000 claims 1
125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims 1
CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 claims 1
150000002430 hydrocarbons Chemical class 0.000 description 24
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 22
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 20
229910052799 carbon Inorganic materials 0.000 description 18
239000012535 impurity Substances 0.000 description 18
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
239000007789 gas Substances 0.000 description 13
229930195734 saturated hydrocarbon Natural products 0.000 description 13
238000004140 cleaning Methods 0.000 description 11
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 10
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 10
239000011949 solid catalyst Substances 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
239000006227 byproduct Substances 0.000 description 9
238000011084 recovery Methods 0.000 description 9
239000012141 concentrate Substances 0.000 description 8
239000000463 material Substances 0.000 description 7
238000000746 purification Methods 0.000 description 7
239000011973 solid acid Substances 0.000 description 7
229930195735 unsaturated hydrocarbon Natural products 0.000 description 7
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 6
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
125000004432 carbon atom Chemical group C* 0.000 description 6
239000000243 solution Substances 0.000 description 6
238000003756 stirring Methods 0.000 description 6
239000000725 suspension Substances 0.000 description 6
150000002576 ketones Chemical class 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
229910052697 platinum Inorganic materials 0.000 description 5
150000001491 aromatic compounds Chemical class 0.000 description 4
229910003460 diamond Inorganic materials 0.000 description 4
239000011521 glass Substances 0.000 description 4
PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 4
229910052737 gold Inorganic materials 0.000 description 4
239000010931 gold Substances 0.000 description 4
238000005342 ion exchange Methods 0.000 description 4
FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
239000000047 product Substances 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
239000002699 waste material Substances 0.000 description 4
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
239000012295 chemical reaction liquid Substances 0.000 description 3
239000012065 filter cake Substances 0.000 description 3
238000005470 impregnation Methods 0.000 description 3
239000000203 mixture Substances 0.000 description 3
229910052759 nickel Inorganic materials 0.000 description 3
239000000843 powder Substances 0.000 description 3
238000007670 refining Methods 0.000 description 3
229910001220 stainless steel Inorganic materials 0.000 description 3
239000010935 stainless steel Substances 0.000 description 3
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
239000004215 Carbon black (E152) Substances 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
244000061458 Solanum melongena Species 0.000 description 2
235000002597 Solanum melongena Nutrition 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
229910017052 cobalt Inorganic materials 0.000 description 2
239000010941 cobalt Substances 0.000 description 2
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
238000011437 continuous method Methods 0.000 description 2
IIEWJVIFRVWJOD-UHFFFAOYSA-N ethylcyclohexane Chemical compound CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 2
239000004744 fabric Substances 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
238000007654 immersion Methods 0.000 description 2
239000011261 inert gas Substances 0.000 description 2
UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
125000002950 monocyclic group Chemical group 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
239000002798 polar solvent Substances 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
229910052703 rhodium Inorganic materials 0.000 description 2
239000010948 rhodium Substances 0.000 description 2
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
238000000967 suction filtration Methods 0.000 description 2
KNPRLIQQQKEOJN-UHFFFAOYSA-N tri(propan-2-yloxy)bismuthane Chemical compound [Bi+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] KNPRLIQQQKEOJN-UHFFFAOYSA-N 0.000 description 2
AMXLSXXWUVANCC-UHFFFAOYSA-N 1h-indole;naphthalene Chemical compound C1=CC=C2NC=CC2=C1.C1=CC=CC2=CC=CC=C21 AMXLSXXWUVANCC-UHFFFAOYSA-N 0.000 description 1
JNRLEMMIVRBKJE-UHFFFAOYSA-N 4,4'-Methylenebis(N,N-dimethylaniline) Chemical compound C1=CC(N(C)C)=CC=C1CC1=CC=C(N(C)C)C=C1 JNRLEMMIVRBKJE-UHFFFAOYSA-N 0.000 description 1
CPGPAVAKSZHMBP-UHFFFAOYSA-N 9-methylanthracene Chemical compound C1=CC=C2C(C)=C(C=CC=C3)C3=CC2=C1 CPGPAVAKSZHMBP-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
241000196324 Embryophyta Species 0.000 description 1
244000061176 Nicotiana tabacum Species 0.000 description 1
235000002637 Nicotiana tabacum Nutrition 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical group [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
229910052921 ammonium sulfate Inorganic materials 0.000 description 1
235000011130 ammonium sulphate Nutrition 0.000 description 1
PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
150000004056 anthraquinones Chemical class 0.000 description 1
150000001463 antimony compounds Chemical class 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
238000005899 aromatization reaction Methods 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
CMWYOMQKNDVFMD-UHFFFAOYSA-N benzene;pentane Chemical compound CCCCC.C1=CC=CC=C1 CMWYOMQKNDVFMD-UHFFFAOYSA-N 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229910052792 caesium Inorganic materials 0.000 description 1
TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
229910000420 cerium oxide Inorganic materials 0.000 description 1
QQZMWMKOWKGPQY-UHFFFAOYSA-N cerium(3+);trinitrate;hexahydrate Chemical compound O.O.O.O.O.O.[Ce+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O QQZMWMKOWKGPQY-UHFFFAOYSA-N 0.000 description 1
239000007810 chemical reaction solvent Substances 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
238000005260 corrosion Methods 0.000 description 1
230000007797 corrosion Effects 0.000 description 1
238000004042 decolorization Methods 0.000 description 1
239000003599 detergent Substances 0.000 description 1
238000010981 drying operation Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000005265 energy consumption Methods 0.000 description 1
238000003912 environmental pollution Methods 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000007429 general method Methods 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
239000008187 granular material Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
125000000468 ketone group Chemical group 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
229910044991 metal oxide Inorganic materials 0.000 description 1
150000004706 metal oxides Chemical class 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
239000011259 mixed solution Substances 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
229910052762 osmium Inorganic materials 0.000 description 1
SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
238000012805 post-processing Methods 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000004064 recycling Methods 0.000 description 1
229910001415 sodium ion Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000007711 solidification Methods 0.000 description 1
230000008023 solidification Effects 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000010025 steaming Methods 0.000 description 1
238000000859 sublimation Methods 0.000 description 1
230000008022 sublimation Effects 0.000 description 1
238000001291 vacuum drying Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/54—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings
- C07C13/605—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings with a bridged ring system
- C07C13/615—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings with a bridged ring system with an adamantane ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/22—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by isomerisation
- C07C5/27—Rearrangement of carbon atoms in the hydrocarbon skeleton
- C07C5/29—Rearrangement of carbon atoms in the hydrocarbon skeleton changing the number of carbon atoms in a ring while maintaining the number of rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/14—Purification; Separation; Use of additives by crystallisation; Purification or separation of the crystals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2529/00—Catalysts comprising molecular sieves
- C07C2529/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites, pillared clays
- C07C2529/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- C07C2529/18—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the mordenite type
- C07C2529/20—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the mordenite type containing iron group metals, noble metals or copper
- C07C2529/22—Noble metals

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Organic Chemistry (AREA)
Crystallography & Structural Chemistry (AREA)
Engineering & Computer Science (AREA)
Analytical Chemistry (AREA)
Oil, Petroleum & Natural Gas (AREA)
Water Supply & Treatment (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

TW092120550A 2002-07-29 2003-07-28 Process for the preparation of adamantane TW200403205A (en)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
JP2002219176A JP4170696B2 (ja)	2002-07-29	2002-07-29	アダマンタン類の製造方法
JP2002220612A JP4170697B2 (ja)	2002-07-30	2002-07-30	高純度アダマンタン類の製造方法
JP2002220613A JP4170698B2 (ja)	2002-07-30	2002-07-30	高純度アダマンタン類の製造方法
JP2002220614A JP4170699B2 (ja)	2002-07-30	2002-07-30	高純度アダマンタン類の製造方法

Publications (2)

Publication Number	Publication Date
TW200403205A TW200403205A (en)	2004-03-01
TWI341832B true TWI341832B (fr)	2011-05-11

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Application Number	Title	Priority Date	Filing Date
TW092120550A TW200403205A (en)	2002-07-29	2003-07-28	Process for the preparation of adamantane

Country Status (6)

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US (1)	US20060111596A1 (fr)
EP (1)	EP1538139A4 (fr)
KR (1)	KR100973879B1 (fr)
CN (1)	CN1671636A (fr)
TW (1)	TW200403205A (fr)
WO (1)	WO2004011405A1 (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2005058779A1 (fr) *	2003-12-17	2005-06-30	Idemitsu Kosan Co., Ltd.	Procede de production d'adamantane
JP2005247702A (ja) *	2004-03-01	2005-09-15	Idemitsu Kosan Co Ltd	アダマンタンの製造方法
JP2007302589A (ja) *	2006-05-10	2007-11-22	Idemitsu Kosan Co Ltd	アダマンタン類の製造方法
EP2017001A4 (fr) *	2006-05-10	2010-09-15	Idemitsu Kosan Co	Procédé de traitement d'une suspension de cristaux
RU2486169C2 (ru) *	2011-03-15	2013-06-27	Учреждение Российской Академии Наук Институт Нефтехимии И Катализа Ран	Способ получения 1-хлорадамантана
CN112851459A (zh) *	2021-01-16	2021-05-28	太原理工大学	一种稠环芳烃制备烷基金刚烷的方法

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Publication number	Priority date	Publication date	Assignee	Title
US3944626A (en) *	1973-04-26	1976-03-16	Kosaku Honna	Process for producing adamantane compounds
JPS5538935B2 (fr)	1973-08-01	1980-10-07
JP2001151706A (ja) *	1999-11-24	2001-06-05	Mitsubishi Gas Chem Co Inc	アダマンタンの分離精製方法
JP2005247702A (ja) *	2004-03-01	2005-09-15	Idemitsu Kosan Co Ltd	アダマンタンの製造方法

2003
- 2003-07-25 CN CNA038180855A patent/CN1671636A/zh active Pending
- 2003-07-25 EP EP03771336A patent/EP1538139A4/fr not_active Withdrawn
- 2003-07-25 US US10/522,338 patent/US20060111596A1/en not_active Abandoned
- 2003-07-25 KR KR1020057001529A patent/KR100973879B1/ko not_active Expired - Fee Related
- 2003-07-25 WO PCT/JP2003/009444 patent/WO2004011405A1/fr not_active Ceased
- 2003-07-28 TW TW092120550A patent/TW200403205A/zh not_active IP Right Cessation

Also Published As

Publication number	Publication date
CN1671636A (zh)	2005-09-21
WO2004011405A1 (fr)	2004-02-05
EP1538139A4 (fr)	2007-07-11
TW200403205A (en)	2004-03-01
EP1538139A1 (fr)	2005-06-08
US20060111596A1 (en)	2006-05-25
KR20050078662A (ko)	2005-08-05
KR100973879B1 (ko)	2010-08-03

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Date	Code	Title	Description
2015-02-11	MM4A	Annulment or lapse of patent due to non-payment of fees

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